The proposed research will focus on chemical models for intermediates in the hydroxylation of proline, and aliphatic oxidation carried out in living organisms by the iron dependent enzyme, prolyl hydroxylase. The relatively recent discovery that this enzyme can decarboxylate 2-ketoglutaric acid (alpha KG) in the absence of proline prompts the basis for this proposal that the exothermic decarboxylation is energetically coupled to the efficient production of a reactve oxo-iron intermediate, responsible for the hydroxylation. Unlike known chemical models, which utilize various combinations of iron and oxygen, and which all suffer from low mass yields of hydroxylation products, the proposed reagents will include alpha KG.